Failure and success both inflate your value (despite what you may think)
And why trying is the only way to build personal capital.
The other day on a call, a tired founder friend said to me “what’s the point in trying to do this when there’s a high likelihood I’ll fail?”.
I instantly felt my body temp skyrocket like a volcano about to blow. In full eruption mode, I began internally screaming…
“What’s the point in trying? WHAT’S THE POINT IN TRYING? Are you crazy?! There are points. MANY points. There aren’t enough years left in my life to list out all the reasons for you!”
It was in this split second of violently self combusting that I realised just how deeply I care about this stuff. I live for trying! I shout about it! Internally! Externally! Incessantly! I think I get so riled up because giving stuff a red hot go has completely changed my life. A few cases in point:
In my early twenties I put my hands up for roles and projects that stretched me way beyond my capability, and the payoff was travelling around the world for work: living in Japan and Singapore, traipsing to New York multiple times a year, and flying to Amsterdam to Bangkok to Paris to Barcelona to suss out my employer’s competition.
Over the past 2 years I’ve thrown myself into sharing online, even though at times it has felt impossible to continue, and my imperfect (but doggedly consistent) writing practice has opened doors to worlds I never knew existed.
All throughout 2025 I’ve launched offers before I felt ready (do we ever?) and have subsequently expanded my earning capacity and impact well beyond what I thought was possible.
Trying hard has led to success over the course of my career but I’d be lying if I said that things have always worked out well. My first business didn’t unfold the way I hoped. I’ve experienced months of zero cash flow and nothing in the pipeline. I’ve been stung by sharp barbs from online trolls and had fleeting moments of questioning whether wandering off the conventional career path was a mistake.
But looking back, even when I felt like a giant walking billboard for being a spectacular flop, I was still growing my personal net worth. With every failed and foiled attempt, I added extra layers of knowledge, skills and experience. Every experiment made me sharper. Every mistake increased my value.
Here's what I now know to be true: giving stuff a go doesn’t only make you smarter (although it certainly does that), it makes you richer. Every time you shoot your shot your personal capital grows.
This idea solidified for me recently when my friend Michelle Battersby (co-founder of a recently acquired startup called Sunroom) put it into words on her IG account. She wrote:
“For those of you who are scared to start a business or make a change, I’d always told myself it doesn’t matter whether your company fails, flatlines, sells or IPOs, you come out the other side with more to offer and a chance to go again. You’ll have inflated your own personal value on the other side. You’ll be smarter, wiser, more experienced.”
Boy oh boy, she is right.
Being courageous inflates your personal value. It builds your intellectual capital (you know what works and develop better judgement), creative capital (you learn how to generate ideas that will take off), reputational capital (people know you’re a cool cat who can deliver and/or peel yourself from the floor to go again) and economic capital (you can command higher rates or seek out bigger roles because you’ve already been in the arena).
Even when things go tits up, your portfolio grows. You become more sought after. You find yourself at bigger tables. You can hold your own in rooms with people who previously had no idea you were there.
This is why second-time founders find it easier to raise money. It’s why experienced startup operators - even from businesses that have gone bust - get hired quickly. It’s why scrappy, imperfect, cringe-worthy creators build authority and get access to locked rooms.
Trying hard is a growth strategy.
Trying hard is THE growth strategy.
Trying hard is the ONLY growth strategy there is.
If you succeed, you build personal capital and win. If you fail, you build personal capital and therefore win. Both outcomes inflate your value. Both outcomes result in quantum leaps. Both outcomes lead to bigger and brighter things.
So there I was, still mid-rant (internally, at least). The neurotransmitters in my brain zapped fervently, racing through every example, every proof point and every argument I could construct for why trying is never wasted.
My founder friend sat there patiently, or perhaps exhausted, waiting for my answer. I took a deep breath and paused to let my simmering blood return to a non-life threatening temperature, and leaned casually across the table.
“What’s the point in trying?”, I played her question back.
“How much time do you have?”
Some early evening thoughts about the economic and financial value of trying hard (and failing) ✌🏼
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Needed to read this today! Thank you!
So true! It's the potential regret that gets me... I'd prefer to try and fail, than never try and look back and wonder what if.